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2,3-diaryl thiazolidinone compound and analogue, and purpose thereof in preparing antiangiogenic drugs

A technology based on thiazolinone and thiazolinone, which is applied in the field of 2,3-diarylthiazolinone compounds and analogs, can solve the problems of easy recurrence, large side effects, genetic instability of cancer cells and easy mutation, etc. question

Active Publication Date: 2012-11-21
BIORAY LABORATORIES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional surgical treatment, radiotherapy and chemotherapy are all aimed at the cancer cells themselves, and cancer cells are prone to mutations due to genetic instability, resulting in drug resistance. Therefore, traditional treatment methods often have large side effects and unsatisfactory curative effects. Easy to relapse and other defects

Method used

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  • 2,3-diaryl thiazolidinone compound and analogue, and purpose thereof in preparing antiangiogenic drugs
  • 2,3-diaryl thiazolidinone compound and analogue, and purpose thereof in preparing antiangiogenic drugs
  • 2,3-diaryl thiazolidinone compound and analogue, and purpose thereof in preparing antiangiogenic drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Example 1-12-(3-bromophenyl)-3-(2-methoxyphenyl)-4-thiazolinone

Embodiment 1-1

[0127] Take the compound 3-bromobenzaldehyde (185mg, 1.0mmol) and o-methoxyaniline (113μL, 1.0mmol) in toluene, under a nitrogen atmosphere, stir in an ice bath for 5min, then change to an oil bath and heat to reflux, The device is connected with an oil-water separator. When anhydrous is produced, cool down after completion, add the compound thioglycolic acid (70 μL, 1.0 mmol) and continue heating to reflux. After the water separation is completed, the crude product is obtained. After purification by column chromatography, the compound AGT001 (309 mg, yield: 85% ): 1 H NMR(400MHz,DMSO)δ7.52(s,1H),7.34(d,J=8.0Hz,1H),7.19(dd,J=8.0,8.0Hz,1H),7.09(dd,J=8.0, 8.0Hz,1H),6.92(d,J=8.0Hz,1H),6.87-6.80(m,2H),6.02(s,1H),3.94(AB,J=15.6Hz,1H),3.86(AB, J=15.6Hz,1H),3.81(s,3H). 13 C NMR (100MHz, CDCl 3 )δ 171.3, 154.9, 141.7, 132.1, 130.9, 130.1, 130.0, 129.8, 126.5, 125.3, 122.5, 121.0, 112.1, 64.1, 55.8, 33.1.

[0128] The preparation of AGT002-AGT067 thiazolinone compounds shown in Ex...

Embodiment 2

[0140] Purpose and principle: MTS assay was used in the cell proliferation experiment. The MTS assay is an assay that uses a colorimetric method to determine the number of cell proliferation in living cells. NADPH dehydrogenase converts MTS tetrazolium salt compound into a colored substance - formazan, which is soluble in tissue culture medium, and its color depth is highly correlated with the number of living cells within a certain range. This model can be used to evaluate the effect of drugs on cell proliferation.

[0141] Method: Human umbilical vein endothelial cells were added to the 96-well plate, and the control group and sample addition group were set up. The sample addition group was added with the compound to be tested at a final concentration of 40 micromolar. After incubation for 60-72 hours, the cell proliferation detection reagent was added and incubated. After 1-3 hours, detect the light absorbance at 490 nm with a microplate reader.

[0142] Results and evalu...

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PUM

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Abstract

The invention discloses a 2,3-diaryl thiazolidinone compound shown in a structural formula (I), a hydrate and pharmaceutically acceptable salts thereof, and a pharmaceutical composition containing the compound, as well as the application of the compound in preparing drugs capable of treating related diseases caused by all kinds of pathological angiogenesis.

Description

technical field [0001] The present invention relates to a class of 2,3-diarylthiazolinone compounds and analogues, and the compounds or the pharmaceutical composition containing the compounds can be used as drugs for treating diseases related to angiogenesis. The invention also relates to a preparation method of the thiazolinone compound. Background technique [0002] Angiogenesis refers to the process of forming new blood vessels on the basis of existing blood vessels, which is a multi-step complex process. Angiogenesis not only plays an important role in physiological processes such as individual development and injury repair, but also is related to angiogenesis eye diseases, diabetic retinopathy, malignant tumors, psoriasis, and rheumatoid arthritis caused by the disruption of angiogenesis balance in pathological processes. , degenerative arthritis and atherosclerosis and other diseases are directly related. [0003] Neovascularization is a common pathological change of...

Claims

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Application Information

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IPC IPC(8): C07D277/14C07D277/38C07D417/04C07D279/06A61K31/426A61K31/506A61K31/4439A61K31/4709A61K31/54A61P27/02A61P9/10A61P27/06A61P35/00A61P29/00A61P19/02A61P17/06A61P3/10
Inventor 易正芳童为光翟东赖力吴婧陈益华刘明耀
Owner BIORAY LABORATORIES INC
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